I Figure 8 shows the generation of an E/Z mixture of alkene I via an E2 reaction. The major E alkene product can undergo a subsequent organocatalysed reaction, via an enamine intermediate, to give final product L, Figure 8. MsO H NO₂ NE₂ C8H7NO2 H E2 I (E/Z mixture) *CO,H H J KH C10H11 NO3 L ee > 95% Figure 8 Page 4 of 5 (i) (ii) (iii) (iv) Draw the structure of both alkene products I and explain the origin of the E- selectivity in the E2 reaction shown in Figure 8; use a reaction coordinate diagram to illustrate your answer. Draw the structure of product L, Figure 8. Discuss the catalytic cycle for the generation of compound L from the E isomer of alkene I, Figure 8; include mechanisms for key steps in the catalytic cycle. Explain the enantioselectivity of the organocatalysed reaction that generates compound L in Figure 8.
I Figure 8 shows the generation of an E/Z mixture of alkene I via an E2 reaction. The major E alkene product can undergo a subsequent organocatalysed reaction, via an enamine intermediate, to give final product L, Figure 8. MsO H NO₂ NE₂ C8H7NO2 H E2 I (E/Z mixture) *CO,H H J KH C10H11 NO3 L ee > 95% Figure 8 Page 4 of 5 (i) (ii) (iii) (iv) Draw the structure of both alkene products I and explain the origin of the E- selectivity in the E2 reaction shown in Figure 8; use a reaction coordinate diagram to illustrate your answer. Draw the structure of product L, Figure 8. Discuss the catalytic cycle for the generation of compound L from the E isomer of alkene I, Figure 8; include mechanisms for key steps in the catalytic cycle. Explain the enantioselectivity of the organocatalysed reaction that generates compound L in Figure 8.
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.SE: Something Extra
Problem 30MP: The carbocation electrophile in a Friede1-Crafts reaction can be generated by an alternate means...
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Transcribed Image Text:I
Figure 8 shows the generation of an E/Z mixture of alkene I via an E2
reaction. The major E alkene product can undergo a subsequent
organocatalysed reaction, via an enamine intermediate, to give final product
L, Figure 8.
MsO
H NO₂
NE₂
C8H7NO2
H
E2
I (E/Z mixture)
*CO,H
H
J
KH
C10H11 NO3
L
ee > 95%
Figure 8
Page 4 of 5
(i)
(ii)
(iii)
(iv)
Draw the structure of both alkene products I and explain the origin of the E-
selectivity in the E2 reaction shown in Figure 8; use a reaction coordinate
diagram to illustrate your answer.
Draw the structure of product L, Figure 8.
Discuss the catalytic cycle for the generation of compound L from the
E isomer of alkene I, Figure 8; include mechanisms for key steps in the
catalytic cycle.
Explain the enantioselectivity of the organocatalysed reaction that generates
compound L in Figure 8.
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